Secondary and tertiary j-amino



Reissued Feb. 9, 1943 UNITED STATES PATENT OFFICE SECONDARY AND TERTIARY S-AMINO- BIETHYL-POLYHYDROXY-PHTHALIDES Walter Siegfried Loewe, New

Neumann, Scarsdale, N. Y.

signor to Walter Rochelle, N. Y., as-

No Drawing. Original No. 2,268,990, dated January 6, 1942, Serial No. 291,30 Application for reissue June 4, August 22, 1939. 8, 1942, Serial No.

4 Claims. (Cl. 260-344) 3 amino methyl polyhydroxy organic bases.

I have discovered that the primary and the mono-methyl amines of this class of chemicals tious diseases, and the like.

My novel compounds can be expressed by the general formula:

where R may be hydrogen, alkyl or aryl radical, R may be aryl or alkyl with more than one carbon atom, and any two or three R" H, the remaining R" A convenient method Mitchells reagent.

Example II.Method of preparing 3-(benzylaminomethyl) -5,7-hydroxy-phthalide.

17 gm. of 2,4-hydroxybenzoic acid, 15 gm. 01' benzylaminoacetaldehyde, 300 cc. of glacial acetic concentrated hydrochloric acid and 30 cc. of water are heated together for about fifteen hours at C. The mixture is evaporated, the residue dissolved in water, filtered, and the base precipitated from the filtrate by amwhen added to the solution of the base in a dilute hydrochloric acid, produces a reddish-brown precipitate.

Example IIL-Method for preparing 3-(di-nbutyl) -aminomethyl-4,5,B-hydroxy-phthalide.

11.5 gm. of gallic acid, 12 gm. of di-n-butyl- 300 cc. of glacial acetic acid, 93 cc.

brownish powder.

The foregoing description of ployed is merely illustrative of the invention.

polyhydroxy-phthalides, as, for example, substitution of monoor di-alkyl or -aryl-amine in place of the halogen in halogenmethyl-polyhydroxy-phthalides, without departing from the spirit of my invention as set forth in the appended claims.

I claim as my 1. A substance represented by the formula:

invention and salts thereof where R is taken from the group consisting of H, alkyl and aryl radicals contain ing not more than 6 carbon atoms, R. is taken from the group consisting of aryl and alkyl radicals having at least two carbon atoms, and not more than 6 and at least two and no more than three R" are OH, the remaining being H. said substance being prepared as a therapeutic agent.

2. A compound of the group consisting in 3- (n-propyl-aminomethyl) -4,5 ,6 hydroxy-phthalide and salts thereof, said compound being preared as a therapeutic agent.

3. A compound of the group consisting in 3- (benzylaminomethyl) 5,7 hydroxy phthalide and salts thereof, said compound being prepared as a therapeutic agent.

'4. A compound of the group consisting in 3- (di n butyl') aminomethyl 4,5,6 hydroxyphthal-ide and salts thereof, said compound being therapeutic agent.

WALTER SIEGFRIED LOEWE.

prepared as a 

